It is strongly advised that you wear a life jacket while wakeboarding though it is not required in some areas. Many more experienced riders wear non coast guard approved vest. These vest still provide some flotation but not as much as a normal coast guard approved jacket. They are wore to allow the rider more flexibility.
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Yes, you do have to wear a life jacket while kayaking, it's "kayaking safety 101". They make them with lighter material now and better fitting to enable the paddler more mobility.